Maybe read the Fair Housing and landlord/tenant laws and see if you are exempt as you say "first-time landlord" and there are certain exclusions if you have, I believe, less than 4 properties and manage them yourself.  

Below is a quote from the county property appraiser: "The cap only applies to the portion of the property receiving homestead exemption.

@Charlotte Raycraftunless your transaction is exempt, agents can't write lending terms into a real estate contract anymore.

He may have applied for an exemption because he is disabled which does qualify him for a tax break. 

@Valerie Naglein my area, when exemptions are removed from a property it greatly increases the amount of tax that would be paid. 

When a tax-exempt entity is engaging in a business on a regular or repeated basis, and therefore competing with tax-paying businesses, there is a trust tax known as UBIT that is incurred - as a way to level the playing field.  

I would check the RLTO on the first item, that may not be allowed in Chicago.The refusing entry is addressed in the RLTO and the summary has to be included with every lease.If you are owner occupied under 6 units you are exempt from the RLTO but I always suggest every landlord use a RLTO compliant lease like the 35 page CAR one that includes everything you need

This number would be reduced by the standard deduction of $12,600 and then further reduced by the exemptions amount of $8,000.

@Kyle Grimm  check with your state division of mortgage lending.many states have exemptions for 1 or 2 transactions a year etc.in our state you can do 2 a year and no more than 3 held at anyone time.those doing above that they deem in the business and needing licensure.

If this has been his primary residence for the past 2 years then he can take the capital gains exemption without the complication and cost of the 1031 Exchange.